Resolution and absolute stereochemistry of 6,7-dimethoxy-4-phenyl- 1,2,3,4-tetrahydroisoquinoline. The crystal structure of the R-hydrochloride salt form.

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dc.contributor.authorMondeshka D.
dc.contributor.authorAngelova I.
dc.contributor.authorStensland B.
dc.contributor.authorWerner P.E.
dc.contributor.authorIvanov C.
dc.date.accessioned2024-11-13T14:47:18Z
dc.date.accessioned2024-11-14T07:25:56Z
dc.date.available2024-11-13T14:47:18Z
dc.date.available2024-11-14T07:25:56Z
dc.date.issued1992-01-01
dc.description.abstractStereospecific multistep synthesis and resolution of 6,7-dimethoxy-4- phenyl-1,2,3,4-tetrahydroisoquinoline (3) has been achieved from its racemic base. The absolute configurations of the optical antipodes converted into their hydrochloride salt forms have been determined by X-ray diffractometric analysis, thus permitting assignment of the antipodes as the (+)-(4R)-3 and (-)-(4S)-3 enantiomers. The crystal structures of the two enantiomers are related as mirror images and only the (4R)-3.HCl form has been fully determined by three-dimensional X-ray diffraction. In the solid state, the carbon atoms of the two methoxy groups deviate slightly from the benzene-ring plane and the chirally oriented phenyl substituent is almost perpendicularly tilted out of conjugation with the isoquinoline system. Examination of the enantiomers in several biochemical tests for 5-HT, NE and DA uptake inhibition-activity revealed an exclusive preference for the (4S)-enantiomer. These results are in accord with previous suggestions that the S-configurational state of the 4-phenyl substituent is important for biological activity.
dc.identifier.doi10.3891/acta.chem.scand.46-0054
dc.identifier.issn0904-213X
dc.identifier.scopusSCOPUS_ID:0026444687en
dc.identifier.urihttps://rlib.uctm.edu/handle/123456789/1470
dc.language.isoen
dc.source.urihttps://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=0026444687&origin=inward
dc.titleResolution and absolute stereochemistry of 6,7-dimethoxy-4-phenyl- 1,2,3,4-tetrahydroisoquinoline. The crystal structure of the R-hydrochloride salt form.
dc.typeArticle
oaire.citation.issue1
oaire.citation.volume46
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